Hellhounds On My Trail
by gardenghost
Summary: My version of what happened when Castiel raised Dean from Hell and how their relationship grows throughout the hardships. Rated M for later chapters


**Dean POV**

I crouched down and leaned against an old and rusting dumpster, trying to catch my breath. I looked around at where I was. It looked like an old worn down factory that had been out of business for at least twenty years or so. Fence lined the perimeter, and where I was scrunched down hiding was right by said fence.

I was breathing too hard, I'm sure the hounds could hear me from a mile away. I knew I was running from the inevitable, but I still had to try. I had to try for my brother, I was the only family he had left.

As minutes passed and I didn't hear anything, I began to relax, tricking myself into believing that maybe I had out-run the hellhounds. Everything was quiet. Then it hit me. A very old memory of my father teaching me the basics of hunting the evils of the world. I remember him elaborating on exactly what was happening now. When everything was dead silent, when not even a cricket chirps or a bird sings, the beast is near.

I stiffened, now smelling the sulfur that I had somehow managed to miss, knowing that I didn't out run anything. The hounds were probably right behind me, waiting for me to start the chase again.

I slowly turned around, and sure enough, I was eye-level with three massive black wolves with burning pupil-less red eyes. Their muzzles were wrinkled in the beginnings of a snarl, yellow foam and saliva were dripping from their mouth's. I was absolutely terrified. As I looked into the eyes of these menacing beasts, it was like I was taken back to the dreadful day I made the deal.

_I put my fake FBI I.D. into the box that contained the skull of a black cat, an ancient coin, and a few hellebore plants. I put the box back in the ground and covered it with the gray gravel that was its resting place. I waited…nothing happened. _

_ I looked around at the four streets of the cross road that I was standing in the middle of, and not a demon in sight. Anger and desperation overtook me. I _needed _this deal to save my brother, and no one was going to stop me from doing it…not even if I had to drag the demon out myself. _

_ "C'mon you vultures! I know you're out there! I want to make a deal!" _

_ Still no response. It was starting to infuriate me._

_ "HEY! Come and get me you evil bastards!"_

_I stood there, just waiting for something to happen. But all that I was met with was dead silence of the night. I couldn't believe it. Not one single demon was coming to get my soul…I mean, I figured my soul was like a wet dream to them, after every one of them that my family and I killed…_

_ A frigid gust of wind blew across my face and the acrid smell of sulfur invaded my nose. It was here. _

_ "Well, well, well…look at what the cat dragged in. Another Winchester! And what can I do for you big boy?"_

_I turned around and was faced with a very sexy woman in a _very _tight black dress with a slit going up the leg. Well…they definitely knew how to pick their vassal's._

_"I want my brother."_

_The demon's eyebrows quirked up and a smirk crossed her face, "Well! I never knew you two were like _that_! But hey, there is plenty of room for a soul damned for incest. In fact, I believe there is a circle especially for that."_

_ I glared at the demon with disgust, "You know what I meant. You get my soul if you bring my brother back. That is all I want."_

_ The she-demon looked me over in a way that made me thoroughly uncomfortable, but I kept my cool so she couldn't see how she was affecting me. She looked my up and down once more, then shook her head._

_ "As much as that offer appeals to me, my boss would not approve of it. I can't."_

_ That was the final straw, there was just too much weighing down on me from the day…I snapped._

_ "LISTEN TO ME BITCH! I had to watch my brother get stabbed to death and then I held him as he bled out his life. I held him as he died. HE IS DEAD! And I am not leaving until he is back and breathing! So I don't give a rats ass what your boss would like or not like…MAKE THE DAMN DEAL!"_

_ I took a shuttering breath. I felt some relief at letting all that out, everything that had been weighing me down for hours. But the sadness and despair was still fresh and not going away. Not until Sam was alive._

_ The demon seemed to contemplate her choices. She still shook her head after a minute._

_ "Look, I would, but it's just not in my interest to disobey this order from the boss. If I were to make the deal and bring Sam back I would have so many demons coming for my blood…I wouldn't last a day."_

_ I finally couldn't hold back my anger and I grabbed her slender neck and held tight._

_ "Like I said, I don't give a RAT'S ASS! I WANT MY BROTHER BACK!" _

_ She nodded vigorously and I let her go. She gasped for air and stepped back. _

_"Alright, let's get this going! My soul for my brother's life. NOW!"_

_The demon glared at me, "Fine__.__ But I can't offer you the same thing as I woulld any other client.__" _

_I returned her glare ten-fold and clenched my teeth, trying to hold back my anger, "What do you _mean_ you can't give me the same deal."_

_ She rolled her eyes and shook her head, "Well…you are Dean Winchester…notorious demon hunter and all that jazz…I can't just let you _live _and give you your precious little Sammy as well…We are going to have to cut down the time…to say…an hour."_

_ I couldn't hold back my anger anymore, "WHAT! AN HOUR! Every other deal was made with ten years to live! No, if you are going to cut my time give me at least five years. That's half."_

_ She shook her head, "No can do buck-o. However, I might be able to up the time to one year."_

_ I looked at her in disbelief. One year…one year to spend with Sam before I get dragged to Hell. I took a deep, steading breath, and nodded. _

_With a smirk she strutted towards me and yanked my face to hers and began kissing me. If it was any other woman I wouldn't have a problem with it. But this was a demon…a disgusting, soul-less, evil monster…and she was making out with me. _

_I shoved her away and swiped the back of my hand across my lips, trying to get the demon germs off of them. I really wished for a tooth brush right then…_

_ "God! What the hell was that for! Now I have demon saliva in my mouth…I feel violated!"_

_ The demon rolled her eyes, "The deal was made and sealed."_

_ I looked at her confused. I figured I would have had to slashed my palm for some blood or had to gone through some kind of ritual. Nothing had happened._

_ The demon sighed in frustration, "Crossroad's deals are sealed with a kiss, chuckles. I would have thought you would have known _that _at least, seeing as you have had a few cases with deals involved. Guess you're not as macho and all-knowing as I originally thought."_

_ I glared at her, "Well you could have warned me before I got lip molested!"_

_ She smirked, "Oh Dean, you know you liked it."_

_ And with I final wink, she was gone. _

I was brought back to reality when a feeling of complete lightness took over me and the next thing I know I am standing in front of my brother...and that demon bitch Ruby.

"Dean! Jesus, are you ok! I thought Ruby hadn't gotten the spell done in time to save you, but I guess I was wrong. We had no idea where you were, so she had to try and find you through the hell hounds that were hunting you. Apparently any demon who knows what they're doing can do it. Man I am glad we got to you in time!"

I stood motionless as Sam came over and hugged me. It wasn't because I wasn't happy to be alive...it was just-

"Damn! I can see why you chose that pretty little blonde as your meat-suit! You're hideous!"

Ruby gave me a pissed off look, "You know, a simple thank you would have been fine. I did just save your life!"

"Wait...you can see what she looks like? Like, her true form?" Sam asked incredulously.

I nodded, "Yeah, and be lucky that you can't, 'cause _damn_! I feel sick just looking at her!"

Ruby stalked over to me and jabbed a finger to my chest, "Listen here chuckles! Don't screw with me today, okay?! I am not in the mood! In case you've forgotten, we still have to hunt down one of the most powerful demons in Hell because _you _decided to sell _your soul_ to Lilith in the _first damn place_! This means I am risking myself for yours again! So I don't think I deserve your sarcasm!"

I was shocked. I might have actually hurt her feelings...oh this was going to be fun!

"Awww, did I hurt poor wittle demon's feelings?"

Ruby growled at me...actually _growled_! "You know what! I am going to kick your god da-" She stopped unexpectedly and turned around.

"Uh, boys...I think we have company."

That's when I heard them. Heavy paw-steps coming from the stairs, walking down towards us. I never really bothered to look at the place I was in, but now I notice that it's a two-story house. It looked lived in, so I can only imagine where the owners are. Probably dead. Or worse, being possessed...or dead and possessed.

I was shaken out of my thoughts by a shake on the arm, and my brother talking urgently to Ruby, "Can we out run them, or hide?"

I knew the answer before she even shook her head no. Of course we couldn't, I know because I had already tried that once.

Ruby had a pained look on her face, "The best option I can think of right now is to fight. Dean can see them, and even though you can't see them you can smell them. Plus they aren't the quietest beasts ever; you'll be able to hear them."

Sam nodded like that made sense, even though he looked scared shitless. But something wasn't right with the picture she was painting...then it hit me,

"And where will you be in this plan of action, hmm?"

Ruby smirked and again shook her head, "Boy's c'mon. Do you really think I am going to risk my freedom from hell for you two...especially when there are three hellhounds. Please! The only thing I'll do is wish you luck. So...good luck you two! Hope your deaths aren't too painful!"

With that she smoked out of her meat-suit. I watched with dread as the black demon smoke vanished out of the house, leaving me and Sam alone to deal with the hounds. I turned and looked at my brother, it would probably be the last time that we spoke to one another, so I wanted to make it count.

"Well...I am definitely back on the highway to hell!"

Sam shook his head at me and chuckled, "Seriously Dean...we are probably about to die and the thing that comes out of your mouth is AC/DC!"

I smirked at Sam, "Well...I was going to say that everything that ever happened bad between us is just dust in the wind...but eh, I figured AC/DC better suited what we are up against than Kansas."

Sam looked at me with sympathy and sadness. We both knew my sarcasm and joking was just to cover up the dread that was threatening to over-whelm me. But he didn't say anything about it.

That's about the time they stepped into view. The black wolves rounded the corner and immediately stopped. They looked us up and down with a hungry look in their faces. Sam shifted beside me, trying to look for them. For the first time I think in my life, I was glad I was the only one bearing the burden of having to see something.

Then the chase began. They lunged at us and Sam and I took off running.

"There's a sitting room on the next left with wooden doors. If we can get in there we should be fine."

I nodded. We rounded the corner and sure enough there was the sitting room...and Ruby too. I couldn't believe she actually came back.

"Come on you slow idiots! They are right behind you!"

I didn't question her at all. I could feel the hot breath of the hound's as they got closer. Another small burst of speed and Sam and I reached the room and grabbed the doors. We had them almost closed when the mutts started to try and push their way in. It felt like I was trying to close the door on a two-ton elephant.

They got the door opened slightly more, just enough to stick their snapping jowls in. again I saw the yellow drool and foam and the smell of sulfur and burning, rotting flesh was sickeningly strong.

With one more heave, we got the door closed. Sam pushed his back against it while I quickly grabbed the bag of salt that was in the pocket of my leather jacket and made a line of salt at the door. Immediately, the barking and growling and door banging stoped. It was working...for the time being anyway.

Sam turned and looked at Ruby with a look of shock on his face. "I can't believe that you actually came back!"

It sounded like he was about to hug her even though she had left us in the first place. I turned to confront Ruby too. Oh she was definitely getting a piece of my mind...and maybe a punch too...my frustrations always seemed to come out faster when I got a good punch in, and it had been a while since I last punched, shot, or stabbed the bitch. It was time to let out some much needed stress.

I stalked over to her and stopped right in front of her face. I cocked my fist back and was about to punch her right in her face when it hit me...this wasn't Ruby's face. It was her meat-suit's face, but underneath that...the actual demon wasn't Ruby.

She smiled sweetly, no innocently, at me. And I knew exactly who it was, and she knew that I knew too.

"Sam...get back, it's not Ruby...it's Lilith!"

Sam looked at me with astonishment, then back at Lilith. He took several steps back along with me. Lilith tilted her head to the side as she studied Sam and I.

"Well now boys, I heard you wanted to meet me, and I just couldn't pass up the chance of meeting the two of you! The soul of the Righteous Man that is damned to Hell, and the future King of Hell. My, my...for such high expectations of you both, you are so...puny! So...unprepared! But that really doesn't matter anymore; because I am going to watch my puppies have fun with you-"

She pointed at me, and then turned a hungry gaze at Sam.

"And you...well, I will deal with you _my _way...I haven't had very much fun here lately, having to watch my back since you two and that skank Ruby decided to try and hunt me down. Which by the way, bravo on that. You got very close a few times there. But...I am better at playing hide and seek than you guys are! And guess what...I FOUND YOU!"

With that, she flung her arms out, causing me to go flying across the room and hitting the table on my back. I tried to get back up, but an invisible force held me where I was. I could see Sam though. He was pressed against a wall and stuggling to get out of the vice-like grip of the invisible hands.

Lilith looked around with mirth lighting up her features, as if this were a game. But then again it probably all was just a big game to her anyway. A grandfather clock that had gone unnoticed until now bonged loudly, indicating that it was five-till midnight. Lilith turned her gaze on me, this time instead of looking into her eyes and feeling like I was seeing two different colors, I only saw one, and it was her pure white eyes. Her true eyes were showing. Surprisingly, the pure whiteness scared me more than the black and red that I had seen so many times before on the countless of demons that Sam and I had hunted down and killed. I think it was just the void of any color at all that got to me.

"Well! Five minutes to midnight boys! Let's have some fun shall we?"

Lilith again made a gesture with her hand and the double doors flew open, revealing the three hellhounds. They were sitting patiently by the door, almost like actual dogs. Their muscles began to bunch and ripple when they saw me. It was as if they could smell that my soul was damned to hell. But then again they probably could, seeing as they were meant to hunt down the souls that were sold and drag them to Hell.

A gust of wind blew the line of salt that was the only thing keeping the mutts at bay away. The hounds' muscles became taught with tension. They were ready to kill me and drag my soul down, but they were waiting for the command of their master first.

Lilith turned her head away from the hellhounds and looked at me with a sickening smile and very sweetly said, "Sick 'em boys."

The hounds launched into action. It happened so fast I didn't even have time enough to think before the first searing stab of pain hit me. After that initial wound, all three were on me. I couldn't register anything but the agony of getting ripped to shreds and the sound of what I knew was my skin getting torn off. Soon I felt one get on top of me and start digging my chest. It's razor sharp claws tore the skin and muscle right off, leaving my rib cage open. I was surprised I wasn't dead yet, but I figured it had something to do with Lilith. Probably wanted me to feel as much of the agony as I could possibly stand and then some before she actually let them take my soul.

However, I could feel myself losing consciousness. I looked at Sam one last time and saw that Lilith had her back to me and was facing him. She said something that I couldn't understand and Sam just kept his eyes on me, refusing to look anywhere else. I could see the tears falling from his cheeks and his eyes were so full of horror. I'm not sure what happened next, but she held the palm of her left hand out at Sam and a blinding white light filled the room...and then I was gone.

***LINE BREAK**

**Sam POV**

I watched in horror as my brother got ripped to shreds by the hellhounds. I tried to get out of the invisible bonds that held me to the wall, but it seemed the more I struggled the tighter they got. I couldn't stop the tears that were coming. As hard as I tried, I just couldn't. I watched as an invisible hound started tearing at my brother's chest. Bits of Dean were being flung everywhere by the vicious tearing and ripping. I felt as a few splatters of his blood land on my cheek, almost making me sick. Then Lilith turned to me.

I refused to look anywhere but at Dean. She soon became aggravated at my lack of attention, "SAM! Look at me before I kill you! LOOK AT ME!"

Then she raised her palm to me and then a blinding, searing light appeared. I thought I was dead for certain, but when the light cleared we were both shocked to see I was on the ground crouching low with my hands over my head, and still very much alive.

Lilith, for the first time ever tonight, looked scared.

"H-How did you do that!? It's not possible! You can't still be alive after that! You ca-"

"Well apparently I can." I pulled out the demon killing knife that I had in my back pocket and lunged at her.

Before I could get the knife into her though, she smoked out of the body, leaving a limp and empty meat-suit.

I looked over to where Dean's mauled body now lay. The hounds must have left after they got what they had come for, because I couldn't smell them anymore.

I slowly made my way to where Dean's body was splayed out on the wooden floor. Blood and pieces of flash were all around his body. Skin and muscle was hanging off in certain areas of the body, and in other places the bone was completely protruding or shattered. The sight would have made me sick if it weren't for the heart-wrenching grief that I felt.

I knelt down beside Dean and looked down at him, causing some of my tears to splash his face. His green eyes stared blankly up at me, causing another heart-wrenching bout of grief to come crashing down upon me.

I felt as though the world weighed down on me in that moment. I couldn't do anything but continue to stare into my brother's dead eyes.

***LINE BREAK**

**Dean POV **

The sweltering heat was the first thing that registered. Then it was the smell. It was god-awful! A mixture of rotting flesh, burning flesh, and sulfur. It made me want to gag. Then as my senses slowly began to kick in, I felt pain. Gut-wrenching pain coming from everywhere on my body.

It was then I realized that there were thick curving hooks embedded into my skin. And connected to those hooks were thick metal chains that were pulled tight, and that seemed to go on forever.

The slide of a knife made me turn my head to the side. A disgusting demon smiled back at me. Its flesh was falling off its face in flakes and blood and puss leaked out of holes in his arms and face. Needless to say, the sight scared me shitless.

But nothing could have prepared me for its voice.

"Hello, I am Alastair...and welcome to the rack. Now, there are a few simple rules that you must follow...well more like tips on how to make your damnation a little less...damnable. One, don't try to escape, if you do, your torture sessions will become even worse than they already are going to be...and trust me, you don't want that. And two, every day, before I start the sessions, I will ask you a simple yes or no question, and the answer you give will either get you off the rack, or will keep you on, enduring the same thing over and over again."

I tried to mask the fear I was feeling...but by the widening smile on the bastards face, I'd say I failed.

"So! Let's get this ball rolling shall we?! Now the question that will be asked of you every day is a simple one...Will you start the torture on the souls that are on this rack along with you? Will you be the one who gives the first cut or removes the first finger? Remember, the answer 'yes' will get you off the rack, while the answer 'no' will keep you on...your choice."

I didn't even have to think about an answer, it just came out.

"You know what you asshole; you can just stick it where the sun shines, 'cause I'm not going to become your little bitch. I'll stay right here, thanks."

Alastair looked over-joyed with the answer I gave, he even clapped his hands once.

"I was hoping you would say that! I am really going to enjoy torturing you, boy. After all the trouble you caused everyone here, I was told to make it as...unbearable...as possible. And I plan on doing just that."


End file.
